A Local’s Guide to Southold

Heading to Southold this summer? Here’s everywhere to eat, drink, and explore once you get there.

For this North Fork native, Southold never used to seem like much of a destination. There was that brief period in high school when I had some friends there, went to some beach parties, and the TCBY opened (remember the original frozen yogurt trend?), but otherwise downtown Southold was not much to speak of. Times have changed. The village now has lots of delicious, interesting food, cute shops to browse and occasional open mics and live music! Plus, there’s more parking and less crowds than there are in (my beloved hometown) Greenport.

To Stay

If you’re feeling fancy: North Fork Table and Inn

Located in an historic inn, North Fork Table continues the tradition with a Manhattan-style twist.  Elegantly refinished rooms with queen size beds and Bigelow’s body products make your country stay luxurious. Run by restaurateurs with experience at Gramercy Kitchen, the food is amazing and inspired. The staff works closely with local farms and the food reflects that relationship. It’s a short walk to Deep Roots Farm, where you can see some of that food being grown (including happy chickens and pigs!), as well as to downtown and the beach.

If you’re feeling fancier: Shorecrest Bed and Breakfast

This B&B was originally the summer home of a New Jersey doctor and retains the original private beaches.  The innkeeper keeps a flock of laying hens which lay colorful eggs. Multi-course breakfasts with all the fixings are served in the formal 1860s dining room on vintage china accented with fresh flowers.  Hammocks, Adirondack chairs, gardens and access to both the Long Island Sound and Arshamomoque Inlet make this a dream spot.

To Eat

Good morning from me and Emily's half eaten flapjacks 🥞

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For breakfast: North Fork Roasting Company

The folks at NoFoRoCo roast their own coffee, and they are serious about it. They’re equally serious about tea (check out the tea garden out back) and food (note the farm gardens out front). My usual is a latte, hot or iced, or the coldbrew. I’ll often pair it with the duck egg burrito or the smoked salmon tartine with horseradish creme fraiche.

For a snack: Blue Duck Bakery

Treat yourself to a cookie and a drink at the Blue Duck, where everything is made in the bakery out back. Take home a pie, cake, or pastry, or bring a loaf of bread to the beach to accompany some farm fresh provisions. The bakery stocks a nice selection of New York state juices and Long Island iced teas (the kid friendly kind!) to accompany their goodies.

For lunch: Wednesday’s Table

Head over to Wednesday’s Table and sit outside with a banh mi, either lemongrass chicken or roast pork. Order it mild, unless you really like things hot!  If you dare, pair it with a spicy hot chocolate.

Hey now, hey now this is what dreams are made of #cacioepepe

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For dinner: Caci

This high-end Italian spot is one of the newest restaurants on the North Fork, and it hasn’t disappointed. The menu changes seasonally, and features local as well as international ingredients and drinks.  Keep an eye out for their series of winemaker dinners, where the chef prepares a special multi-course dinner to go with selected wines from a local vineyard.

To Do

For local culture: Taps and Corks

This cute wine and beer bar serves mostly local libations, with a great selection and reasonable prices.  The vibe is laid-back, and there’s wifi, so you might find locals getting work done on their laptops while sipping glasses of sauvignon blanc. Since they don’t serve food, just free pretzels to go with the beer, the barkeep doesn’t mind if you bring in a pizza from next door to accompany your drinks. Check out Wednesday’s open mic night for all sorts of talent and laughs.

For antiques: Lost and Found

A step up from the North Fork’s many thrift shops, Lost and Found is a curated yet casual antique store.  Founded by a father-and-son team of professional yard salers who also run a tag sale business, the shop is a showcase for some of their treasures. It’s not your typical cluttered antique shop housing only things older than your grandparents and pricier than they would approve of. There’s space and clean white walls, and the contents change often. The vibe is younger, with items from the sixties, seventies, and eighties mingling with older pieces. Prices are reasonable, and like at any good yard sale, on occasion you find a sweet deal!

For the view: Horton Point Lighthouse

Built in 1857, the lighthouse was restored in the nineties and now houses a nautical museum. On weekends from Memorial Day through Columbus Day, you can tour the lighthouse and climb the spiral stairs to the top, where there’s a clear view of Connecticut across the Long Island Sound. Bring lunch to eat at the outdoor tables on the grounds or climb the stairs down to the beach.

Summer love #northfork 😍🍅

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For local food: The Farm

If you want to take some of the best of the North Fork home with you, stop by KK’s, The Farm, on the eastern edge of town. This beautiful biodynamic farm is home to fruits, vegetables, flowers, bees and farmer Ira and friends. Depending on availability and time of year, the stand out front or the barn down the driveway may be stocked with fresh baby greens (that will last, so don’t be afraid to travel with them), shiso pesto, tomato sauce, pickled dilly beans, garlic, floral bouquets, local eggs, seedlings and more.

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Lily Dougherty-Johnson is a native North Forker, finally pursuing a lifelong dream of farming. She writes from her home in Greenport, New York, with her reluctant farmdog snoring by her side.